164530-42-1

Upstream product

• 924-44-7 glyoxylic acid ethyl ester 
• 24424-99-5 di-tert-butyl dicarbonate 
• 56613-80-0 D-2-phenylglycinol 

Downstream Products

• 234122-92-0 (2R,4R)-3-tert-butoxycarbonyl-2-(4-tert-butyldimethylsilyloxy-but-2-ynoil)-4-phenyl-1,3-oxazolidine 
• 179600-33-0 [2R,2(1S),4R]-3-tert-butoxycarbonyl-2-(4-tert-butyldimethylsilyloxy-1-hydroxy-but-2-ynyl)-4-phenyl-1,3-oxazolidine 
• 179600-37-4 (4R,9S,9aS)-9-Benzyloxy-4-phenyl-3,4,9,9a-tetrahydro-6H-pyrido[2,1-c][1,4]oxazin-1-one 
• 179600-36-3 (2R,3S)-3-Benzyloxy-1-((R)-2-hydroxy-1-phenyl-ethyl)-1,2,3,6-tetrahydro-pyridine-2-carbonitrile 
• 209003-90-7 (2R,4R,1'R)-2-(1'-benzyloxy-4'-oxobutyl)-4-phenyloxazolidine-3-carboxylic acid tert-butyl ester 
• 211861-29-9 (2R,4R,1'S)-2-(1'-benzyloxy-4'-oxobutyl)-4-phenyloxazolidine-3-carboxylic acid tert-butyl ester 
• 209003-89-4 (2R,4R,1'S)-2-(1'-benzyloxy-pent-4'-enyl)-4-phenyloxazolidine-3-carboxylic acid tert-butyl ester 
• 211861-24-4 (2R,4R,1'R)-2-(1'-benzyloxy-pent-4'-enyl)-4-phenyloxazolidine-3-carboxylic acid tert-butyl ester 
• 211861-23-3 (2R,4R,1'R)-2-(1'-hydroxy-pent-4'-enyl)-4-phenyloxazolidine-3-carboxylic acid tert-butyl ester 
• 209003-88-3 (2R,4R,1'S)-2-(1'-hydroxy-pent-4'-enyl)-4-phenyloxazolidine-3-carboxylic acid tert-butyl ester 
• 211861-27-7 (2R,4R,1'R)-2-(1'-benzyloxy-4'-hydroxyhexadecyl)-4-phenyloxazolidine-3-carboxylic acid tert-butyl ester 
• 209003-91-8 (2R,4R,1'R)-2-(1'-benzyloxy-4'-oxohexadecyl)-4-phenyloxazolidine-3-carboxylic acid tert-butyl ester 
• 211861-26-6 (3R,5S,8R,8aR)-8-Benzyloxy-5-dodecyl-3-phenyl-hexahydro-oxazolo[3,2-a]pyridine-5-carbonitrile 
• 211861-30-2 (2R,4R,1'S)-2-(1'-benzyloxy-4'-hydroxyheptyl)-4-phenyloxazolidine-3-carboxylic acid tert-butyl ester 

Relevant academic research and scientific papers

Cyclization of a chiral oxazolidine as a key-step for the synthesis of functionalized piperidines

Bicyclic oxazolidine 6, a potential precursor for the synthesis of enantiopure piperidines and indolizidines, was synthesized from (R)-phenylglycinol. A stereoselective addition of cyanide anion on this compound afforded ultimately (2S,3S)-3-hydroxypipecolic acid 9.

N-Boc 2-acyloxazolidines: Useful precursors to enantiopure 1,2-diols via highly diastereoselective nucleophilic additions

N-Boc 2-Acyloxazolidines were synthesized from norephedrine and phenylglycinol. This preparation involves: (i) a transformation or the above β-amino alcohols into N-Boc 2-ethoxycarbonyloxazolidines, (ii) the formation of the corresponding Weinreb amides and, (iii) a reaction between these amides and organometallic reagents. Such diastereomerically pure heterocycles react cleanly with various nucleophilic reagents (Grignard reagents, sodium borohydride and allylsilane) to afford the corresponding alcohols. Treatment of these hydroxyoxazolidines with trifluoro acetic acid, followed by hydrolysis and reduction of the intermediate α-hydroxy aldehydes afforded 1,2-diols. The overall transformation exhibited in most cases a complete diastereoselectivity which can be explained by a chelated model for the nucleophilic addition.